Forest Hill's Jeff Judge in The Wall Street Journal: How to talk to your parents about money without shutting

By Jeff Judge, CFP®, AEP®, ChFC®, CLU®, Managing Partner, Chesapeake Financial Planners, Forest Hill, MD.

Almost every family I work with in Harford County reaches this conversation eventually. A parent is aging, the paperwork is somewhere, and nobody wants to be the one who brings it up.

When The Wall Street Journal asked me about it, my answer was about tone before content. The fastest way to end the conversation is to make it about what you stand to inherit. The moment a parent hears entitlement, their defenses go up, and you may not get a second try.

So make it about them. Ask what care they want. Ask who they want making decisions if they cannot make them. Then start small: which bills do you pay, which accounts do you have, who holds them. The will, the power of attorney, and long-term care can wait for the third or fourth conversation. If a parent will not talk at all, hand them a form to fill out privately. They do not have to show it to you. They only have to tell you where it lives.

The local version of this is specific. I see it with families in Bel Air whose parents still keep everything in a filing cabinet, with adult children in Fallston who moved back to be closer, and with commuters from Perry Hall who get two or three weekends a year at that kitchen table. The window is shorter than it looks.

One general takeaway, and this is education rather than individualized advice: have the first conversation while both generations can still shape the outcome. After a medical event, the useful options narrow quickly.

This piece builds on "Talking to Your Aging Parents About Money," in The Wall Street Journal (September 2026).

Jeff Judge, CFP®, AEP®, ChFC®, CLU®, is Managing Partner at Chesapeake Financial Planners in Forest Hill, MD. Book an intro call.